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Showing NP-Card for 3,4-dichloro-5-hydroxy-5h-furan-2-one (NP0312411)

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Record Information
Version2.0
Created at2022-09-11 09:10:45 UTC
Updated at2022-09-11 09:10:46 UTC
NP-MRD IDNP0312411
Secondary Accession NumbersNone
Natural Product Identification
Common Name3,4-dichloro-5-hydroxy-5h-furan-2-one
Description3,4-Dichloro-5-hydroxy-2,5-dihydrofuran-2-one belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. 3,4-dichloro-5-hydroxy-5h-furan-2-one is found in Lessingianthus linearis. 3,4-Dichloro-5-hydroxy-2,5-dihydrofuran-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0312411 (3,4-dichloro-5-hydroxy-5h-furan-2-one)


  Mrv1533004241514192D          

  9  9  0  0  0  0            999 V2000
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  9  1  0  0  0  0
M  END
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3D MOL for NP0312411 (3,4-dichloro-5-hydroxy-5h-furan-2-one)

     RDKit          3D

 11 11  0  0  0  0  0  0  0  0999 V2000
    1.5684   -2.2307   -0.0358 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8325   -1.2099    0.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4951   -1.1909    0.4343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9140    0.1431    0.3670 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9673    0.2403   -0.5665 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2529    0.9338   -0.0987 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2326    2.6499   -0.3414 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2842    0.1327   -0.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9015    0.5976   -0.8469 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2162    0.5550    1.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4795   -0.6210   -0.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2  8  1  0
  8  9  1  0
  8  6  2  0
  6  7  1  0
  6  4  1  0
  5 11  1  0
  4 10  1  1
M  END
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3D SDF for NP0312411 (3,4-dichloro-5-hydroxy-5h-furan-2-one)


  Mrv1533004241514192D          

  9  9  0  0  0  0            999 V2000
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0312411

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1OC(=O)C(Cl)=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C4H2Cl2O3/c5-1-2(6)4(8)9-3(1)7/h3,7H

> <INCHI_KEY>
ZAKLKBFCSHJIRI-UHFFFAOYSA-N

> <FORMULA>
C4H2Cl2O3

> <MOLECULAR_WEIGHT>
168.96

> <EXACT_MASS>
167.9380993

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
12.374098125990551

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4-dichloro-5-hydroxy-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
0.42

> <JCHEM_LOGP>
0.7981070626666666

> <ALOGPS_LOGS>
-0.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.987698012838486

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.5612521196458

> <JCHEM_PKA_STRONGEST_BASIC>
-4.692492904517686

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
31.784800000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.97e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4-dichloro-5-hydroxy-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0312411 (3,4-dichloro-5-hydroxy-5h-furan-2-one)

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PDB for NP0312411 (3,4-dichloro-5-hydroxy-5h-furan-2-one)
HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.306   1.175   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    8 Cl   UNK     0      -1.651   1.651   0.000  0.00  0.00          Cl+0
HETATM    9 Cl   UNK     0      -0.615  -1.536   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    9                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7                                                            
CONECT    9    6                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END

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3D PDB for NP0312411 (3,4-dichloro-5-hydroxy-5h-furan-2-one)
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SMILES for NP0312411 (3,4-dichloro-5-hydroxy-5h-furan-2-one)
OC1OC(=O)C(Cl)=C1Cl
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INCHI for NP0312411 (3,4-dichloro-5-hydroxy-5h-furan-2-one)
InChI=1S/C4H2Cl2O3/c5-1-2(6)4(8)9-3(1)7/h3,7H
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Synonyms
ValueSource
3,4-Dichloro-5-hydroxy-2(5H)-furanoneMeSH
3,4-(Dichloro)-5-hydroxy-2(5H)-furanoneMeSH
3,4-MAMeSH
MCA CPDMeSH
Chemical FormulaC4H2Cl2O3
Average Mass168.9600 Da
Monoisotopic Mass167.93810 Da
IUPAC Name3,4-dichloro-5-hydroxy-2,5-dihydrofuran-2-one
Traditional Name3,4-dichloro-5-hydroxy-5H-furan-2-one
CAS Registry NumberNot Available
SMILES
OC1OC(=O)C(Cl)=C1Cl
InChI Identifier
InChI=1S/C4H2Cl2O3/c5-1-2(6)4(8)9-3(1)7/h3,7H
InChI KeyZAKLKBFCSHJIRI-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Lessingianthus linearisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassDihydrofurans  
Sub ClassFuranones  
Direct ParentButenolides  
Alternative Parents
Substituents
  • 2-furanone
    • 

  • Vinylogous halide
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Carboxylic acid ester
    • 

  • Chlorohydrin
    • 

  • Halohydrin
    • 

  • Hemiacetal
    • 

  • Lactone
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Chloroalkene
    • 

  • Haloalkene
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Vinyl chloride
    • 

  • Vinyl halide
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Organohalogen compound
    • 

  • Organochloride
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.42ALOGPS
logP0.8ChemAxon
logS-0.53ALOGPS
pKa (Strongest Acidic)10.56ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity31.78 m³·mol⁻¹ChemAxon
Polarizability12.37 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound91487  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]